p-Aminoacetophenone → 4'-Acetyl-4-formylbenzanilide

HRID 480962Notes

Reaction equation

HRID 480962 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:18]([C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1)=[O:19]>>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][C:20]([CH:18]=[O:19])=[CH:21][CH:22]=2)=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 3

HCID 7468p-AminoacetophenoneHCID 8471TriethylamineHCID 124246204-Formylbenzoyl chloride

Product 1

HCID 187663244'-Acetyl-4-formylbenzanilideYield 90%

Procedure

In the same manner as that described in Example 1(1), a reaction was carried out using commercially available p-aminoacetophenone (309 mg, 2.3 mmol), triethylamine (0.48 ml, 3.4 mmol), and 4-formylbenzoyl chloride (500 mg, 3.0 mmol) and the reaction mixture was treated according to a similar procedure to that described in Example 1(1) to afford a crystalline residue which was recrystallized from a mixture of tetrahydrofuran and hexane to give 4′-acetyl-4-formylbenzanilide (552. mg, yield 90%) as pale yellow powdery crystals.

Workup

  1. additionthe reaction mixture was treated
  2. customto afford a crystalline residue which
  3. customwas recrystallized from a mixture of tetrahydrofuran and hexane

Sources & evidence

ORD record
ord-c3ae990f97b44f3ca4a104e8111a7862
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

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